p-Toluenesulfonic acid monohydrate → HCID 21877772, compound

Participants

Reaction Steps

A stirred solution of 4-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-2,6-difluorophenyl]tetrahydro-2H-thiopyran-4-ol (Step 2, 1.617 g, 5.00 mmol) and p-toluenesulfonic acid monohydrate (0.107 g) in benzene (20 mL) is heated at reflux using a Dean-Stark trap for 5 h, during which additional p-toluenesulfonic acid monohydrate (0.342 g) is added. Solvent is then removed under reduced pressure, and the residue is taken up in CH2Cl2 (60 mL), washed with saturated aqueous NaHCO3 (2×20 mL) and water (3×20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by chromatography on a Biotage Flash 40M 90 g silica gel cartridge, eluting with 2-5% EtOAc/Hexanes, affords the title compound, mp 118-119° C.; MS (ESI+) for C17H17F2NS m/z 306 (M+H)+.

Provenance & Evidence